US3658952A - Bis((dialkyl)phosphonoalkylamido) alkyls - Google Patents
Bis((dialkyl)phosphonoalkylamido) alkyls Download PDFInfo
- Publication number
- US3658952A US3658952A US838329A US3658952DA US3658952A US 3658952 A US3658952 A US 3658952A US 838329 A US838329 A US 838329A US 3658952D A US3658952D A US 3658952DA US 3658952 A US3658952 A US 3658952A
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- US
- United States
- Prior art keywords
- parts
- formula
- phosphorus
- formaldehyde
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 125000000217 alkyl group Chemical group 0.000 title description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 50
- 239000007795 chemical reaction product Substances 0.000 abstract description 24
- 229920003180 amino resin Polymers 0.000 abstract description 10
- CLNYPSIJBWKTKL-UHFFFAOYSA-N (1-amino-1-oxopropan-2-yl)phosphonic acid Chemical compound NC(=O)C(C)P(O)(O)=O CLNYPSIJBWKTKL-UHFFFAOYSA-N 0.000 abstract description 9
- 229920002678 cellulose Polymers 0.000 abstract description 6
- 239000001913 cellulose Substances 0.000 abstract description 6
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract description 2
- 239000002657 fibrous material Substances 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 150000001875 compounds Chemical class 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 229910052698 phosphorus Inorganic materials 0.000 description 21
- 239000011574 phosphorus Substances 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 239000000463 material Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- -1 2-chlorethyl Chemical group 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000002759 woven fabric Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- 229930040373 Paraformaldehyde Natural products 0.000 description 4
- 229920000297 Rayon Polymers 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 229920002866 paraformaldehyde Polymers 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- MCONGYNHPPCHSD-UHFFFAOYSA-N 3-dimethoxyphosphoryl-n-(hydroxymethyl)propanamide Chemical compound COP(=O)(OC)CCC(=O)NCO MCONGYNHPPCHSD-UHFFFAOYSA-N 0.000 description 2
- LSCSYJWMZUCJDW-UHFFFAOYSA-N 3-dimethoxyphosphorylpropanamide Chemical compound COP(=O)(OC)CCC(N)=O LSCSYJWMZUCJDW-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- SYDYRFPJJJPJFE-UHFFFAOYSA-N [[4,6-bis[bis(hydroxymethyl)amino]-1,3,5-triazin-2-yl]amino]methanol Chemical compound OCNC1=NC(N(CO)CO)=NC(N(CO)CO)=N1 SYDYRFPJJJPJFE-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine powder Natural products NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 1
- LJZOTLVPIGKBBG-UHFFFAOYSA-N 2-(dimethoxyphosphorylmethyl)-3-hydroxypropanamide Chemical compound COP(=O)(OC)CC(C(=O)N)CO LJZOTLVPIGKBBG-UHFFFAOYSA-N 0.000 description 1
- ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2 ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 0.000 description 1
- CVKGSDYWCFQOKU-UHFFFAOYSA-N 2-n-butyl-1,3,5-triazine-2,4,6-triamine Chemical compound CCCCNC1=NC(N)=NC(N)=N1 CVKGSDYWCFQOKU-UHFFFAOYSA-N 0.000 description 1
- YLIOJOOKMJEHJM-UHFFFAOYSA-N 3-diethoxyphosphorylpropanoic acid Chemical compound CCOP(=O)(OCC)CCC(O)=O YLIOJOOKMJEHJM-UHFFFAOYSA-N 0.000 description 1
- NNTWKXKLHMTGBU-UHFFFAOYSA-N 4,5-dihydroxyimidazolidin-2-one Chemical compound OC1NC(=O)NC1O NNTWKXKLHMTGBU-UHFFFAOYSA-N 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- NJYZCEFQAIUHSD-UHFFFAOYSA-N acetoguanamine Chemical compound CC1=NC(N)=NC(N)=N1 NJYZCEFQAIUHSD-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- MASBWURJQFFLOO-UHFFFAOYSA-N ammeline Chemical compound NC1=NC(N)=NC(O)=N1 MASBWURJQFFLOO-UHFFFAOYSA-N 0.000 description 1
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- ARZLUCYKIWYSHR-UHFFFAOYSA-N hydroxymethoxymethanol Chemical group OCOCO ARZLUCYKIWYSHR-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
- D06M13/288—Phosphonic or phosphonous acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
- C08K5/5353—Esters of phosphonic acids containing also nitrogen
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S260/00—Chemistry of carbon compounds
- Y10S260/24—Flameproof
Definitions
- reaction products containing phosphorus, from (a) a condensation product of (a') 50 to 100 mol percent of at least one compound of formula are preferred, wherein R denotes a methyl or ethyl residue and X and n have the significance indicated.
- Particularly suitable phosphonopropionic acid amides are also those of formula wherein R R and n have the significance indicated and X denotes a hydrogen atom or a methyl group.
- R R R and R each denote an alkyl, halogenalkyl or alkenyl residue having at most 4 carbon atoms each, (h) formaldehyde or a reagent which releases formaldehyde and (c) optionally an alkanol having at most 4 carbon atoms.
- reaction products containing phosphorus are probably essentially phosphonopropionic acid amides of formula wherein R R R R and X have the significance indicated.
- Phosphonopropionic acid amides of formula wherein n denotes 1 or 2 are of very particular interest.
- R R R and R can thus all be identical, partially identical with one another or all different from one another.
- R and R and/or R and R denote two identical residues of the composition indicated.
- R and R can again be mutually different or preferably identical.
- n-propyl, isopropyl, ethyl, methyl, allyl or chloralkyl groups such as 2-chlorethyl or 2,3-dichloropropyl groups may be mentioned.
- X can for example represent a n-butyl, ethyl or methyl group.
- Phosphonopropionic acid amides wherein X denotes a methyl group or especially a hydrogen atom should however be highlighted.
- reaction products containing phosphorus can be manufactured according to usual methods which are in themselves known, by reacting the condensation product (a) with formaldehyde or with a reagent releasing formaldehyde at elevated temperature, optionally in the presence of a basic catalyst, and optionally subsequently further eth erifying it with an alcohol of formula wherein X represents an alkyl residue having at most 4 carbon atoms.
- a compound of Formula 3 is obtained if a compound of formula of very particular interest if compounds of Formula 8 are used.
- the pI-Lvalue of the aqueous preparations containing the phosphorus-containing reaction products or the compounds of Formula 3 is advantageously less than 5.
- strong mineral acids such as sulphuric acid, nitric acid or preferably hydrochloric acid wherein R R R R and n have the significance indicated is reacted in the indicated manner with formaldehyde or with a reagent releasing formaldehyde and is optionally subsequently further etherified with an alcohol of Formula 9.
- reaction of the condensation product (a) or of a compound of Formula with formaldehyde or with a reagent releasing formaldehyde such as for example paraformaldehyde advantageously takes place at temperatures up to 150 C., preferably at 50 to 100 C.
- This reaction is optionally carried out in the presence of a basic catalyst.
- a basic catalyst Possible catalysts are both strong bases such as for example sodium or potassium hydroxide or sodium methylate and also weak bases such as for example sodium acetate, magnesium carbonate or especially magnesium oxide.
- the amount of the monomethylol compound formed can be determined by determining the formaldehyde bonded as CH OH. As a rule the yields of monomethylol compound are 80 to 97%.
- Compounds of Formula 3 wherein R represents an alkyl residue having at most 4 carbon atoms are obtained by etherification of the monomethylol compound with a monohydric aliphatic alcohol which contains at most 4 carbon atoms, in the presence of an acid.
- the starting substances of Formula 10 wherein 11:1 are obtained by condensation of equimolar amounts of at least one compound of formula Rr-O CHg-CH:CONH2 with a compound of formula wherein R R R and R have the significance indicated, with warming, appropriately in the presence of an organic solvent which forms an azeotrope with water, such as for example benzene or toluene.
- the starting substances of Formula 10 are obtained by condensation of 2 molecules of a compound of Formula 12 again with warming and appropriately in the presence of an organic solvent which forms an azeotrope with water.
- the invention also relates to a process for the flameproofing of fibre materials containing cellulose, characterised in that an aqueous preparation which contains at least one phosphorus-containing reaction product of the indicated composition, or a phosphonopropionic acid amide of Formula 3, and optionally a curable aminoplast precondensate, is applied to these materials, and that the materials are thereafter dried and subjected to a treatment at elevated temperature.
- the phosphorus-containing reaction products or the phosphonopropionic acid amides of Formula 3 are used for fiameproofing textile material containing cellulose.
- Phosphonopropionic acid amides of Formulae 3 to 7 are preferred, and the process for fiameproofing is are added to the preparations.
- the acids themselves, especially hydrochloric acid it is also possible to use compounds from which the corresponding acids are easily formed in water by hydrolysis, for example even without warming.
- Phosphorus trichloride phosphorus pentachloride, phosphorus oxychloride, thionyl chloride, sulphuryl chloride, cyanuryl chloride, acetyl chloride and chloracetyl chloride may here be mentioned as examples.
- Phosphorus trichloride phosphorus pentachloride, phosphorus oxychloride, thionyl chloride, sulphuryl chloride, cyanuryl chloride, acetyl chloride and chloracetyl chloride may here be mentioned as examples.
- Phosphorus trichloride phosphorus pentachloride, phosphorus oxychloride, thionyl chloride, sulphuryl chloride, cyanuryl chloride, acetyl chloride and chloracetyl chloride may here be mentioned as examples.
- acid decomposition products for example cyanuric acid and hydrochloric acid.
- the prepara tions to be used in accordance with the invention may contain yet further substances.
- An addition of aminoplast pro-condensates is advantageous for achieving a good tflameproofing finish which is wash-fast.
- aminoplast precondensates addition products of formaldehyde to nitrogen compounds capable of methylolation are understood.
- 1,3,5-aminotriazines such as N substituted melamines, for example N-butylmelamine, N- trihalogenomethylmelamines, as well as ammeline, guanamines, for example benzoguanamine, acetoguanamine or also diguanamines may be mentioned.
- thiourea alkylureas or arylureas and alkylthioureas or arylthioureas, alkyleneureas or alkylenediureas, for example ethyleneurea, propyleneurea, acetylenediurea or especially 4,5-dihydroxyimidazolidone-Z and derivatives thereof, for example the 4,5-dihydroxyimidazolidone-2 which is substituted by the residue at the hydroxyl group in the 4-position.
- methylol compounds of a urea, of an ethyleneurea or of melamine are preferentially used.
- Particularly valuable products are in general yielded by products which are as highly methylolated as possible. Both predominantly monomolecular and also more highly pre-condensed aminoplasts are suitable' as component (b). e
- the ethers of these aminoplast pre-condensates can also be employed together with the compounds of Formula 1.
- the ethers of alkanols such as methanol, ethanol, npropanol, isopropanol, n-butanol or pentanols are for cxample advantageous. It is however advantageous for these amrnoplast pre-condensates to be water-soluble, such as for example the pentamethylolmelamine-dimethyl ether.
- the preparations for flameproofing also contam a latent acid catalyst for accelerating 'the cure of the aminoplast pre-condensate and for crosslinking the phosphorus-containing reaction products, or the compounds of Formula 3.
- latent acid catalysts the catalysts known for curing aminoplasts on cellulose-containing material can be used, for example ammonium chloride,
- ammonium dihydrogen orthophosphate magnesium chloride, zinc nitrate and others.
- the preparations contain a copolymer obtainable by polymerisation in aqueous emulsion from (a) 0.25 to 10% of an alkaline earth salt of an u,B-ethylenica1ly unsaturated monocarboxylic acid, (b) 0.25 to 30% of a N-methylolamide or N-methylolamide-ether of an u,/3-ethylenically unsaturated monocarboxylic or dicarboxylic acid and (c) 99.5 to 60% of at least one other copolymerisable compound.
- copolymers and their manufacture are also known.
- the tear strength and abrasion resistance of the treated fibre material can be advantageously influenced by the conjoint use of such a copolymer.
- a plasticising finishing agent for example an aqueous polyethylene emulsion or ethylene copolymer emulsion, should be mentioned.
- the content of phosphorus-containing reaction products or of compound of Formula 3 in the aqueous preparation is appropriately of such magnitude that 10 to 28% are applied to the material to be treated.
- the commercially available textile materials from native or regenerated cellulose can take up between 50 and 120% of an aqueous preparation.
- the amount of the additive which is required to adjust the hydrogen ion concentration to a value of less than 5 depends on the selected value itself and on the nature of the additive, though it is in any case not possible to go below a certain minimum. A certain excess above this minimum amount is generally to be recommended. Large excesses do not offer any advantages and can even prove harmful.
- a polymer of the indicated nature is further added to the preparation, then this is appropriately done in small amounts, for example 1 to relative to the amount of the phosphorus-containing reaction product or of the compound of Formula 3.
- an optional plasticiser where the appropriate amounts can again be 1 to 10%.
- the preparations are now applied to the cellulose-containing fibre materials, for example linen, cotton, acetate rayon, viscose rayon or also fibre mixtures of such mate-.
- rials and others such as Wool, polyamide or polyester fibres, and this application can be effected in a manner which is in itself known.
- piece goods are used and impregnated on a padder of the usual construction, fed with the preparation at room temperature.
- the fibre material impregnated in this way now has to be dried, and this preferably takes place at temperatures up to 100 C. Thereafter it is subjected to a dry heat treatment at temperatures above 100 C., for example between 130 and 200 C., and preferably between 150 and 180 C., the duration of which can be the shorter, the higher the temperature. This duration of heating is for example 2 to 6 minutes at temperatures of 150 to 180 C. Since the rnethylol residues or methylol-ether residues in the phosphorus-containing reaction products or in the compounds of Formula 1 are split during this process, water or an alcohol are at the same time produced. Now it has been found that these volatile decomposition products must be continuously removed from the material in order that the desired effect should be able to manifest itself fully.
- a post-wash with an acid-binding reagent preferably with aqueous sodium carbonate solution, for example at 40 C. up to the boiling point, and for 3 to 10 minutes, is
- EXAMPLE 1 362 parts (2 mols) of 3-dimethylphosphonopropionamide and 422 parts (2 mols) of 3-dimethylphosphonopropionic acid methylolamide are suspended in 1000 parts of toluene in a stirred flask of capacity 2500 parts by volume, provided with a water separator. 4 parts of p-toluenesulphonic acid are further added and the mixture is heated to the boiling point of the toluene, with the Water formed during the condensation being azeotropically removed and collected in the water separator. After 3 /2 hours reaction time no further water is formed. 33 parts of water are obtained (calculated: 36 parts).
- the toluene is thereafter removed in vacuo and 123 parts of 97.5% strength paraformaldehyde (4 mols) and 6 parts of solid sodium methylate are added to the residual melt and the mixture heated for 30 minutes to 100 C. internal temperature whilst stirring, with the Water separator first being replaced by a reflux condenser. The mixture is then cooled to 6065 C. and 800 parts of methanol are added. It is cooled to 10 C. Whilst stirring rapidly and unreacted paraformaldehyde which has separated out is filtered off. The filtrate is evaporated in vacuo at 40 C.
- condensation product obtained above 164 parts (0.4 mol) of the condensation product obtained above are mixed with 30 parts of aqueous formaldehyde (40% strength) (0.4 mol) in a stirred flask of capacity 250 parts by volume provided with a reflux condenser, thermometer and pH-electrode, and are methylolated for 2 hours at 60 C. A pH of 8.5 is maintained through dropwise addition of a total of 2 g. of 30% strength sodium hydroxide solution. After cooling to room temperature 196 parts of a slightly cloudy syrupy solution containing 89 to 90% of active substance are obtained.
- EXAMPLE 4 295 parts of bis-(2-chlorethyl)-phosphonopropionic acid methylolamide (0.95 mol) are suspended in 250 parts of benzene in a stirred flask of capacity 500 parts by volume provided with a water separator, and are heated to the boiling point of the benzene. Within hours a total of 15.5 parts of water are formed (theory: 17 parts), and after this the mixture is cooled to 50 C. and the benzene removed in vacuo.
- the 100% strength product contains one -CH OH group.
- the opalescent syrupy product thus obtained contains almost of active substance and probably corresponds to the formula:
- EXAMPLE 7 A woven cotton fabric is padded with one of the aqueis probably present.
- EXAMPLE 5 211 parts (1 mol) of 3-dimethylphosphonomethylolpropionic acid amide and 181 parts (1 mol) of 3-dimethylphosphonopropionic acid amide are mixed with 250 parts of benzene and 2. parts of p-toluenesulphonic acid in a stirred flask of capacity 500 parts by volume, provided with a water separator, and are heated to the boiling point of benzene. The calculated quantity of Water (18 parts) is obtained over the course of 18 hours condensation time. Thereafter the benzene is removed in ous liquors A and B of the table which follows. The liquor uptake is 80%. Drying is carried out at 70 to 80 C. followed by curing for 4% minutes at C.
- the woven fabric is now post-washed at the boil for 5 minutes in a solution containing 2 g. of anhydrous sodium carbonate per litre, rinsed and dried.
- a part of the Woven fabric is boiled 5 times for 30 minutes in a solution containing 2 g. of sodium carbonate and 5 g. of soap per litre of Water (5 SNV-4 washes).
- Pentamethylolmelamine dimethyl ether 607) 80 Polyethylene emulsion 20% strength), L .i.f. 20 20 TABLE III NH4C1, I! I1 4 4 10 tifil i 1 li e D. en p of the preparation 4 3. 8 Washing Seconds in fffi gf i a After post-washing 0 11 Burning t 0 0 b After 5 SNV3 Washes.-- 0 10. 5 T length (cm 0 3 1L 5 0 After SNV-3 washes 0 ll. 5 After 5 SNV-4 washes: 15
- EXAMPLE 8 A phosphorus-containing reaction product of the formula A woven cotton fabric is padded with one of the aqueous liquors A to D of Table II. The liquor uptake is 1 2 80%. Drying is carried out at 70 to 80 0, followed P CH2O-X1 by curing for 4 /2 minutes at 160 C. The woven fabric 1s now post-washed at the boll for 5 minutes m a solution containing 2 g. of anhydrous sodium carbonate per litre Whfifein 1, 2 1 and 2 6 d n t an alkyl 01 of water, rinsed and dried.
- a part of the woven f b i chloroalkyl radical having at most 4 carbon atoms each is boiled 5 times or 10 times for minutes in a solution 30 or allyl, and X denotes a hydrogen atom or an alkyl containing 2 g, of sodium carbonate and 5 g, of soap er radical having at most 4 carbon atoms and n denotes 1 litre of water ( SNV-4 washes). or 2.
- Phosphorus-containing reaction products according to claim 1 corresponding to the formula R -O ⁇ //O 0 /O-R /P ⁇ CHz-O-Xr /P ⁇ R 0 CH2CHz-CO-NCH2(O-CH2) n-1 HNC 0-CHr-CH3 0R wherein X denotes a hydrogen atom or a methyl group. to DIN 53906) The results of these tests are also sum- 4.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Fireproofing Substances (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1036568A CH498977A (de) | 1968-07-11 | 1968-07-11 | Verfahren zum Knitter- und Flammfestmachen von cellulosehaltigen Textilmaterialien |
Publications (1)
Publication Number | Publication Date |
---|---|
US3658952A true US3658952A (en) | 1972-04-25 |
Family
ID=4362439
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US838329A Expired - Lifetime US3658952A (en) | 1968-07-11 | 1969-07-01 | Bis((dialkyl)phosphonoalkylamido) alkyls |
Country Status (10)
Country | Link |
---|---|
US (1) | US3658952A (fr) |
BE (1) | BE735917A (fr) |
BR (1) | BR6910638D0 (fr) |
CH (2) | CH498977A (fr) |
DE (1) | DE1933479C3 (fr) |
ES (1) | ES369341A1 (fr) |
FR (1) | FR2012718A1 (fr) |
GB (1) | GB1241498A (fr) |
NL (1) | NL6910626A (fr) |
SE (1) | SE359587B (fr) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3754981A (en) * | 1970-06-11 | 1973-08-28 | Ciba Geigy Ag | Process for flameproofing cellulose-containing fibre material |
US3908051A (en) * | 1973-02-28 | 1975-09-23 | Mitsui Toatsu Chemicals | Method for processing cellulose containing materials to impart thereto flame resistance |
US3998789A (en) * | 1973-09-11 | 1976-12-21 | Sumitomo Bakelite Company, Limited | Flame resistant thermosetting resin composition and method for preparing same |
US4026808A (en) * | 1972-03-30 | 1977-05-31 | Hooker Chemicals & Plastics Corporation | Flame retardant textile finishes |
US4125575A (en) * | 1975-07-18 | 1978-11-14 | Compagnie Francaise De Produits Industriels | Phosphonylated amides |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL98728A0 (en) * | 1990-08-03 | 1992-07-15 | Pfersee Chem Fab | Flameproofing compositions containing phosphono compounds and organic acids |
-
1968
- 1968-07-11 CH CH1036568A patent/CH498977A/de not_active IP Right Cessation
- 1968-07-11 CH CH1036568D patent/CH1036568A4/xx unknown
-
1969
- 1969-06-04 SE SE07868/69A patent/SE359587B/xx unknown
- 1969-07-01 US US838329A patent/US3658952A/en not_active Expired - Lifetime
- 1969-07-02 DE DE1933479A patent/DE1933479C3/de not_active Expired
- 1969-07-02 FR FR6922382A patent/FR2012718A1/fr not_active Withdrawn
- 1969-07-04 GB GB33962/69A patent/GB1241498A/en not_active Expired
- 1969-07-10 ES ES369341A patent/ES369341A1/es not_active Expired
- 1969-07-10 BE BE735917D patent/BE735917A/xx unknown
- 1969-07-10 NL NL6910626A patent/NL6910626A/xx unknown
- 1969-07-11 BR BR210638/69A patent/BR6910638D0/pt unknown
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3754981A (en) * | 1970-06-11 | 1973-08-28 | Ciba Geigy Ag | Process for flameproofing cellulose-containing fibre material |
US4026808A (en) * | 1972-03-30 | 1977-05-31 | Hooker Chemicals & Plastics Corporation | Flame retardant textile finishes |
US3908051A (en) * | 1973-02-28 | 1975-09-23 | Mitsui Toatsu Chemicals | Method for processing cellulose containing materials to impart thereto flame resistance |
US3998789A (en) * | 1973-09-11 | 1976-12-21 | Sumitomo Bakelite Company, Limited | Flame resistant thermosetting resin composition and method for preparing same |
US4125575A (en) * | 1975-07-18 | 1978-11-14 | Compagnie Francaise De Produits Industriels | Phosphonylated amides |
Also Published As
Publication number | Publication date |
---|---|
SE359587B (fr) | 1973-09-03 |
NL6910626A (fr) | 1970-01-13 |
BE735917A (fr) | 1970-01-12 |
DE1933479C3 (de) | 1974-04-25 |
GB1241498A (en) | 1971-08-04 |
DE1933479B2 (de) | 1973-08-16 |
BR6910638D0 (pt) | 1973-01-11 |
FR2012718A1 (fr) | 1970-03-20 |
ES369341A1 (es) | 1971-06-01 |
DE1933479A1 (de) | 1970-01-15 |
CH498977A (de) | 1970-07-31 |
CH1036568A4 (fr) | 1970-07-31 |
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